NP-MRD: Showing NP-Card for (1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione (NP0173913)

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Record Information

Version

2.0

Created at

2022-09-03 11:06:30 UTC

Updated at

2022-09-03 11:06:30 UTC

NP-MRD ID

NP0173913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione

Description

CHEMBL3973505 belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Based on a literature review very few articles have been published on CHEMBL3973505.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    5.6732   -0.1803    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7779   -0.6505   -0.5977 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954   -0.4676   -0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298   -1.1490    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4994   -2.3417    1.2936 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1646   -1.0401    0.4515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9400   -0.5972    1.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6716   -2.3276    0.2312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6145   -0.0417   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3621    0.7124   -1.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8256    1.6154   -2.1145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4574    1.8789   -2.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    2.7578   -2.9256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    1.1788   -1.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285    1.4460   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1256    2.4162   -2.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4994    0.7682   -0.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937   -0.1816    0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8444   -0.9050    1.1567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2168   -0.6324    1.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6482   -0.4506    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7614    0.2134   -0.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8291    0.5298   -1.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5355    1.1918   -2.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6908   -0.4667    0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786    0.9357    0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205   -0.6461    1.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3211    0.3220    1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5527   -1.4077    2.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -0.2802    2.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7510   -2.9050    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1061    2.6264   -2.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5805    0.9472   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6717   -0.7528    0.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4594    0.4133    1.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7525   -1.3187    1.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716   -1.2111    1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 17 15  1  0
 15 16  1  0
 15 14  2  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9 22  1  0
 22 21  2  0
  9  6  1  0
  6  7  1  0
  6  8  1  1
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 23  1  0
 23 24  2  0
 21 18  1  0
 22 14  1  0
 23 10  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
 17 33  1  0
 16 32  1  0
 21 37  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END


  Mrv1652309032213062D          

 24 26  0  0  1  0            999 V2000
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9202    1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0017    1.4091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  1  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9 22  1  0  0  0  0
 14 22  1  0  0  0  0
 10 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0173913

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)OC3=C(C2=C1)[C@@](C)(O)C(Cl)=C(OC)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H13ClO7/c1-16(21)10-7-4-6(22-2)5-8(18)9(7)15(20)24-12(10)11(19)13(23-3)14(16)17/h4-5,18,21H,1-3H3/t16-/m1/s1

> <INCHI_KEY>
UMKWAHOXPWRVRW-MRXNPFEDSA-N

> <FORMULA>
C16H13ClO7

> <MOLECULAR_WEIGHT>
352.72

> <EXACT_MASS>
352.0349805

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
32.773022467069524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methyl-1H,4H,6H-benzo[c]chromene-4,6-dione

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
1.7700396729999999

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.623396607516838

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.355456831234186

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8482021130758115

> <JCHEM_POLAR_SURFACE_AREA>
102.28999999999999

> <JCHEM_REFRACTIVITY>
86.421

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0       7.494   3.437   0.000  0.00  0.00          Cl+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.451   3.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.737   2.630   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.414  -1.897   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.494  -1.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   22                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21    9   14                                                  
CONECT   23   10    3   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₃ClO₇

Average Mass

352.7200 Da

Monoisotopic Mass

352.03498 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)OC3=C(C2=C1)[C@@](C)(O)C(Cl)=C(OC)C3=O

InChI Identifier

InChI=1S/C16H13ClO7/c1-16(21)10-7-4-6(22-2)5-8(18)9(7)15(20)24-12(10)11(19)13(23-3)14(16)17/h4-5,18,21H,1-3H3/t16-/m1/s1

InChI Key

UMKWAHOXPWRVRW-MRXNPFEDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
2-benzopyran
Benzopyran
Aryl ketone
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyran
Benzenoid
Vinylogous acid
Vinylogous halide
Tertiary alcohol
Heteroaromatic compound
Chlorohydrin
Halohydrin
Ketone
Lactone
Chloroalkene
Oxacycle
Ether
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Organooxygen compound
Organochloride
Organohalogen compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.62	ALOGPS
logP	1.77	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29814755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24905551

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione (NP0173913)

MOL for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)

3D MOL for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)

3D SDF for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)

3D-SDF for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)

PDB for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)

3D PDB for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)

SMILES for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)

INCHI for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)

Structure for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)

3D Structure for NP0173913 ((1r)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione)